Reaktion #676270

Reaktionsgleichung

2-phenylquinoline

→

desired product

Ausbeute 98.0%

2-Phenyl-1,2,3,4-tetrahydroquinoline

Ausbeute 98.0%

Lösungsmittel

acetic acid

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 3 M sodium hydroxide solution (70 mL), water (20 mL), and brine (20 mL)
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a crude oil
6. 6
   SonstigePurification by flash column chromatography (100% hexanes to 25% ethyl acetate/hexanes)

Vorschrift

A solution of 2-phenylquinoline, (0.248 g, 1.21 mmol) [Aldrich, cat. #299650] in acetic acid (6.0 mL) was treated with borane-pyridine complex (0.605 mL, 5.99 mmol) and stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with 3 M sodium hydroxide solution (70 mL), water (20 mL), and brine (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give a crude oil. Purification by flash column chromatography (100% hexanes to 25% ethyl acetate/hexanes) gave the desired product (0.247 g, 98%) as a racemic mixture. LCMS calculated for C15H16N (M+H)+: m/z=210.1. found: 210.1.

Quelle